Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801001593/na6040sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801001593/na6040Isup2.hkl |
CCDC reference: 159757
All H atoms were located by difference Fourier synthesis and refined with fixed individual displacement parameters [U(H) = 1.5Ueq(Cmethyl) or U(H) = 1.2Ueq(C)] using a riding model with C—H(aromatic) = 0.95, C—H(methyl) = 0.98, C—H(secondary) = 0.99 or C—H(tertiary) = 1.00. A l l hydroxyl H atoms were refined isotropically.
Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991).
Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level. |
C23H28O5·H2O | F(000) = 864 |
Mr = 402.47 | Dx = 1.221 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.948 (1) Å | Cell parameters from 8192 reflections |
b = 27.128 (3) Å | θ = 0–25° |
c = 9.045 (1) Å | µ = 0.09 mm−1 |
β = 94.30 (1)° | T = 173 K |
V = 2189.4 (4) Å3 | Block, colourless |
Z = 4 | 0.70 × 0.65 × 0.45 mm |
Siemens CCD three-circle diffractometer | 4836 independent reflections |
Radiation source: fine-focus sealed tube | 4088 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω scans | θmax = 27.1°, θmin = 2.4° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.941, Tmax = 0.962 | k = −34→34 |
41555 measured reflections | l = −11→11 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0615P)2 + 0.8381P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
4836 reflections | Δρmax = 0.31 e Å−3 |
283 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0036 (10) |
C23H28O5·H2O | V = 2189.4 (4) Å3 |
Mr = 402.47 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.948 (1) Å | µ = 0.09 mm−1 |
b = 27.128 (3) Å | T = 173 K |
c = 9.045 (1) Å | 0.70 × 0.65 × 0.45 mm |
β = 94.30 (1)° |
Siemens CCD three-circle diffractometer | 4836 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 4088 reflections with I > 2σ(I) |
Tmin = 0.941, Tmax = 0.962 | Rint = 0.028 |
41555 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.31 e Å−3 |
4836 reflections | Δρmin = −0.17 e Å−3 |
283 parameters |
Experimental. ; |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.29361 (13) | 0.13075 (4) | 0.54834 (13) | 0.0198 (2) | |
H1 | 0.4034 | 0.1358 | 0.5406 | 0.024* | |
C11 | 0.28443 (13) | 0.08187 (4) | 0.63200 (13) | 0.0194 (2) | |
C12 | 0.15444 (14) | 0.05409 (4) | 0.63776 (13) | 0.0204 (2) | |
O12 | 0.02302 (10) | 0.06934 (3) | 0.57925 (10) | 0.0250 (2) | |
H12 | 0.017 (3) | 0.1092 (10) | 0.565 (3) | 0.094 (8)* | |
C13 | 0.14973 (14) | 0.00474 (4) | 0.71296 (14) | 0.0230 (3) | |
H13A | 0.0811 | −0.0171 | 0.6522 | 0.028* | |
H13B | 0.1074 | 0.0091 | 0.8101 | 0.028* | |
C14 | 0.30308 (15) | −0.02096 (5) | 0.73807 (14) | 0.0240 (3) | |
C17 | 0.35423 (16) | −0.04164 (5) | 0.59148 (15) | 0.0295 (3) | |
H17A | 0.3625 | −0.0146 | 0.5205 | 0.044* | |
H17B | 0.2808 | −0.0658 | 0.5506 | 0.044* | |
H17C | 0.4520 | −0.0577 | 0.6100 | 0.044* | |
C18 | 0.28982 (18) | −0.06367 (5) | 0.84774 (16) | 0.0346 (3) | |
H18A | 0.3870 | −0.0803 | 0.8641 | 0.052* | |
H18B | 0.2146 | −0.0872 | 0.8070 | 0.052* | |
H18C | 0.2594 | −0.0508 | 0.9421 | 0.052* | |
C15 | 0.41524 (15) | 0.01758 (5) | 0.80366 (14) | 0.0253 (3) | |
H15A | 0.3925 | 0.0245 | 0.9071 | 0.030* | |
H15B | 0.5172 | 0.0033 | 0.8068 | 0.030* | |
C16 | 0.41507 (14) | 0.06573 (4) | 0.71962 (13) | 0.0217 (3) | |
O16 | 0.53345 (10) | 0.09202 (3) | 0.73513 (11) | 0.0284 (2) | |
C21 | 0.24629 (14) | 0.17507 (4) | 0.63908 (13) | 0.0224 (3) | |
C22 | 0.35272 (15) | 0.20166 (5) | 0.72617 (14) | 0.0243 (3) | |
O22 | 0.49556 (11) | 0.18933 (4) | 0.74452 (11) | 0.0328 (2) | |
H22 | 0.513 (3) | 0.1514 (11) | 0.730 (3) | 0.105 (9)* | |
C23 | 0.31470 (16) | 0.24720 (5) | 0.81107 (15) | 0.0298 (3) | |
H23A | 0.3997 | 0.2705 | 0.8111 | 0.036* | |
H23B | 0.3025 | 0.2379 | 0.9153 | 0.036* | |
C24 | 0.17178 (16) | 0.27352 (5) | 0.74844 (15) | 0.0300 (3) | |
C27 | 0.1986 (2) | 0.29882 (5) | 0.60019 (17) | 0.0417 (4) | |
H27A | 0.1066 | 0.3155 | 0.5616 | 0.063* | |
H27B | 0.2270 | 0.2740 | 0.5287 | 0.063* | |
H27C | 0.2794 | 0.3231 | 0.6160 | 0.063* | |
C28 | 0.1266 (2) | 0.31269 (6) | 0.86021 (18) | 0.0410 (4) | |
H28A | 0.0356 | 0.3296 | 0.8203 | 0.061* | |
H28B | 0.2079 | 0.3367 | 0.8773 | 0.061* | |
H28C | 0.1076 | 0.2967 | 0.9541 | 0.061* | |
C25 | 0.04799 (16) | 0.23432 (5) | 0.72627 (16) | 0.0311 (3) | |
H25A | 0.0173 | 0.2243 | 0.8248 | 0.037* | |
H25B | −0.0402 | 0.2494 | 0.6713 | 0.037* | |
C26 | 0.09214 (14) | 0.18863 (5) | 0.64370 (14) | 0.0241 (3) | |
O26 | −0.01393 (11) | 0.16289 (4) | 0.58288 (11) | 0.0313 (2) | |
C31 | 0.22749 (13) | 0.13039 (5) | 0.38573 (13) | 0.0218 (3) | |
C32 | 0.21582 (14) | 0.08646 (5) | 0.30472 (13) | 0.0238 (3) | |
H32 | 0.2384 | 0.0560 | 0.3532 | 0.029* | |
C33 | 0.17118 (16) | 0.08683 (5) | 0.15254 (14) | 0.0290 (3) | |
O33 | 0.15874 (14) | 0.04450 (4) | 0.07038 (11) | 0.0417 (3) | |
H33 | 0.174 (3) | 0.0167 (9) | 0.128 (3) | 0.067 (7)* | |
C34 | 0.13794 (18) | 0.13137 (6) | 0.08035 (15) | 0.0367 (3) | |
H34 | 0.1075 | 0.1318 | −0.0225 | 0.044* | |
C35 | 0.14979 (19) | 0.17503 (6) | 0.16041 (16) | 0.0364 (3) | |
H35 | 0.1270 | 0.2054 | 0.1116 | 0.044* | |
C36 | 0.19483 (16) | 0.17490 (5) | 0.31197 (15) | 0.0294 (3) | |
H36 | 0.2033 | 0.2051 | 0.3650 | 0.035* | |
O1W | 0.80268 (13) | 0.03988 (4) | 0.77648 (13) | 0.0409 (3) | |
H1W | 0.720 (3) | 0.0598 (8) | 0.765 (2) | 0.065 (6)* | |
H2W | 0.873 (3) | 0.0512 (9) | 0.708 (3) | 0.077 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0205 (6) | 0.0188 (6) | 0.0202 (6) | −0.0001 (4) | 0.0012 (4) | −0.0001 (4) |
C11 | 0.0224 (6) | 0.0188 (5) | 0.0171 (5) | 0.0014 (4) | 0.0021 (4) | −0.0008 (4) |
C12 | 0.0228 (6) | 0.0223 (6) | 0.0162 (5) | 0.0023 (5) | 0.0015 (4) | −0.0027 (4) |
O12 | 0.0207 (4) | 0.0252 (5) | 0.0289 (5) | −0.0006 (3) | −0.0005 (3) | 0.0012 (4) |
C13 | 0.0256 (6) | 0.0205 (6) | 0.0229 (6) | −0.0018 (5) | 0.0031 (5) | −0.0002 (5) |
C14 | 0.0304 (7) | 0.0203 (6) | 0.0211 (6) | 0.0022 (5) | 0.0015 (5) | 0.0015 (5) |
C17 | 0.0360 (7) | 0.0253 (6) | 0.0277 (7) | 0.0051 (5) | 0.0055 (5) | −0.0017 (5) |
C18 | 0.0477 (9) | 0.0255 (7) | 0.0306 (7) | 0.0024 (6) | 0.0028 (6) | 0.0074 (6) |
C15 | 0.0276 (6) | 0.0247 (6) | 0.0231 (6) | 0.0033 (5) | −0.0024 (5) | 0.0027 (5) |
C16 | 0.0235 (6) | 0.0221 (6) | 0.0195 (6) | 0.0019 (5) | 0.0018 (5) | −0.0031 (5) |
O16 | 0.0214 (4) | 0.0266 (5) | 0.0366 (5) | 0.0005 (4) | −0.0029 (4) | 0.0009 (4) |
C21 | 0.0275 (6) | 0.0189 (6) | 0.0207 (6) | 0.0006 (5) | 0.0009 (5) | 0.0008 (4) |
C22 | 0.0278 (6) | 0.0222 (6) | 0.0229 (6) | −0.0001 (5) | 0.0011 (5) | −0.0001 (5) |
O22 | 0.0284 (5) | 0.0301 (5) | 0.0391 (6) | 0.0015 (4) | −0.0026 (4) | −0.0068 (4) |
C23 | 0.0352 (7) | 0.0258 (7) | 0.0279 (7) | −0.0007 (5) | −0.0005 (5) | −0.0070 (5) |
C24 | 0.0391 (8) | 0.0219 (6) | 0.0288 (7) | 0.0048 (5) | 0.0019 (6) | −0.0053 (5) |
C27 | 0.0664 (11) | 0.0237 (7) | 0.0349 (8) | 0.0039 (7) | 0.0031 (7) | −0.0001 (6) |
C28 | 0.0512 (9) | 0.0308 (8) | 0.0411 (8) | 0.0070 (7) | 0.0043 (7) | −0.0127 (6) |
C25 | 0.0306 (7) | 0.0296 (7) | 0.0333 (7) | 0.0069 (5) | 0.0030 (6) | −0.0052 (6) |
C26 | 0.0270 (6) | 0.0231 (6) | 0.0221 (6) | 0.0016 (5) | 0.0011 (5) | 0.0014 (5) |
O26 | 0.0277 (5) | 0.0279 (5) | 0.0376 (5) | 0.0002 (4) | −0.0017 (4) | −0.0025 (4) |
C31 | 0.0216 (6) | 0.0247 (6) | 0.0191 (6) | 0.0007 (5) | 0.0025 (4) | 0.0014 (5) |
C32 | 0.0268 (6) | 0.0242 (6) | 0.0207 (6) | 0.0023 (5) | 0.0027 (5) | 0.0014 (5) |
C33 | 0.0348 (7) | 0.0320 (7) | 0.0203 (6) | 0.0016 (6) | 0.0038 (5) | −0.0030 (5) |
O33 | 0.0672 (8) | 0.0355 (6) | 0.0221 (5) | 0.0031 (5) | 0.0011 (5) | −0.0060 (4) |
C34 | 0.0499 (9) | 0.0420 (8) | 0.0179 (6) | 0.0061 (7) | 0.0006 (6) | 0.0035 (6) |
C35 | 0.0522 (9) | 0.0315 (7) | 0.0255 (7) | 0.0070 (6) | 0.0027 (6) | 0.0086 (6) |
C36 | 0.0400 (8) | 0.0240 (6) | 0.0242 (6) | 0.0027 (5) | 0.0027 (6) | 0.0018 (5) |
O1W | 0.0325 (6) | 0.0479 (7) | 0.0433 (6) | 0.0122 (5) | 0.0094 (5) | 0.0140 (5) |
C1—C11 | 1.5319 (16) | C23—C24 | 1.5354 (19) |
C1—C21 | 1.5330 (16) | C23—H23A | 0.9900 |
C1—C31 | 1.5437 (17) | C23—H23B | 0.9900 |
C1—H1 | 1.0000 | C24—C25 | 1.538 (2) |
C11—C12 | 1.3903 (17) | C24—C28 | 1.5413 (19) |
C11—C16 | 1.4309 (17) | C24—C27 | 1.541 (2) |
C12—O12 | 1.3193 (15) | C27—H27A | 0.9800 |
C12—C13 | 1.5037 (17) | C27—H27B | 0.9800 |
O12—H12 | 1.09 (3) | C27—H27C | 0.9800 |
C13—C14 | 1.5407 (17) | C28—H28A | 0.9800 |
C13—H13A | 0.9900 | C28—H28B | 0.9800 |
C13—H13B | 0.9900 | C28—H28C | 0.9800 |
C14—C18 | 1.5357 (18) | C25—C26 | 1.5147 (18) |
C14—C15 | 1.5372 (18) | C25—H25A | 0.9900 |
C14—C17 | 1.5405 (18) | C25—H25B | 0.9900 |
C17—H17A | 0.9800 | C26—O26 | 1.2699 (16) |
C17—H17B | 0.9800 | C31—C32 | 1.3989 (17) |
C17—H17C | 0.9800 | C31—C36 | 1.3996 (18) |
C18—H18A | 0.9800 | C32—C33 | 1.4042 (18) |
C18—H18B | 0.9800 | C32—H32 | 0.9500 |
C18—H18C | 0.9800 | C33—O33 | 1.3678 (17) |
C15—C16 | 1.5112 (17) | C33—C34 | 1.395 (2) |
C15—H15A | 0.9900 | O33—H33 | 0.92 (2) |
C15—H15B | 0.9900 | C34—C35 | 1.388 (2) |
C16—O16 | 1.2759 (15) | C34—H34 | 0.9500 |
C21—C22 | 1.3912 (18) | C35—C36 | 1.3996 (19) |
C21—C26 | 1.4312 (18) | C35—H35 | 0.9500 |
C22—O22 | 1.3195 (16) | C36—H36 | 0.9500 |
C22—C23 | 1.5069 (18) | O1W—H1W | 0.92 (2) |
O22—H22 | 1.05 (3) | O1W—H2W | 0.97 (3) |
C11—C1—C21 | 112.78 (10) | C22—C23—C24 | 114.01 (11) |
C11—C1—C31 | 115.74 (10) | C22—C23—H23A | 108.8 |
C21—C1—C31 | 114.43 (10) | C24—C23—H23A | 108.8 |
C11—C1—H1 | 104.0 | C22—C23—H23B | 108.8 |
C21—C1—H1 | 104.0 | C24—C23—H23B | 108.8 |
C31—C1—H1 | 104.0 | H23A—C23—H23B | 107.6 |
C12—C11—C16 | 117.67 (11) | C23—C24—C25 | 107.36 (11) |
C12—C11—C1 | 124.31 (11) | C23—C24—C28 | 109.31 (12) |
C16—C11—C1 | 117.82 (10) | C25—C24—C28 | 109.91 (12) |
O12—C12—C11 | 122.56 (11) | C23—C24—C27 | 110.38 (12) |
O12—C12—C13 | 113.97 (10) | C25—C24—C27 | 110.62 (12) |
C11—C12—C13 | 123.47 (11) | C28—C24—C27 | 109.24 (12) |
C12—O12—H12 | 113.4 (14) | C24—C27—H27A | 109.5 |
C12—C13—C14 | 114.50 (10) | C24—C27—H27B | 109.5 |
C12—C13—H13A | 108.6 | H27A—C27—H27B | 109.5 |
C14—C13—H13A | 108.6 | C24—C27—H27C | 109.5 |
C12—C13—H13B | 108.6 | H27A—C27—H27C | 109.5 |
C14—C13—H13B | 108.6 | H27B—C27—H27C | 109.5 |
H13A—C13—H13B | 107.6 | C24—C28—H28A | 109.5 |
C18—C14—C15 | 110.11 (11) | C24—C28—H28B | 109.5 |
C18—C14—C17 | 108.88 (11) | H28A—C28—H28B | 109.5 |
C15—C14—C17 | 110.63 (11) | C24—C28—H28C | 109.5 |
C18—C14—C13 | 109.00 (11) | H28A—C28—H28C | 109.5 |
C15—C14—C13 | 107.31 (10) | H28B—C28—H28C | 109.5 |
C17—C14—C13 | 110.90 (10) | C26—C25—C24 | 114.72 (11) |
C14—C17—H17A | 109.5 | C26—C25—H25A | 108.6 |
C14—C17—H17B | 109.5 | C24—C25—H25A | 108.6 |
H17A—C17—H17B | 109.5 | C26—C25—H25B | 108.6 |
C14—C17—H17C | 109.5 | C24—C25—H25B | 108.6 |
H17A—C17—H17C | 109.5 | H25A—C25—H25B | 107.6 |
H17B—C17—H17C | 109.5 | O26—C26—C21 | 122.45 (12) |
C14—C18—H18A | 109.5 | O26—C26—C25 | 116.71 (11) |
C14—C18—H18B | 109.5 | C21—C26—C25 | 120.82 (11) |
H18A—C18—H18B | 109.5 | C32—C31—C36 | 118.73 (11) |
C14—C18—H18C | 109.5 | C32—C31—C1 | 120.84 (11) |
H18A—C18—H18C | 109.5 | C36—C31—C1 | 120.00 (11) |
H18B—C18—H18C | 109.5 | C31—C32—C33 | 120.79 (12) |
C16—C15—C14 | 114.70 (10) | C31—C32—H32 | 119.6 |
C16—C15—H15A | 108.6 | C33—C32—H32 | 119.6 |
C14—C15—H15A | 108.6 | O33—C33—C34 | 117.85 (12) |
C16—C15—H15B | 108.6 | O33—C33—C32 | 122.15 (12) |
C14—C15—H15B | 108.6 | C34—C33—C32 | 120.00 (12) |
H15A—C15—H15B | 107.6 | C33—O33—H33 | 112.0 (14) |
O16—C16—C11 | 121.79 (11) | C35—C34—C33 | 119.32 (13) |
O16—C16—C15 | 117.28 (11) | C35—C34—H34 | 120.3 |
C11—C16—C15 | 120.87 (11) | C33—C34—H34 | 120.3 |
C22—C21—C26 | 118.06 (11) | C34—C35—C36 | 120.93 (13) |
C22—C21—C1 | 120.33 (11) | C34—C35—H35 | 119.5 |
C26—C21—C1 | 121.52 (11) | C36—C35—H35 | 119.5 |
O22—C22—C21 | 123.72 (12) | C31—C36—C35 | 120.23 (12) |
O22—C22—C23 | 113.41 (11) | C31—C36—H36 | 119.9 |
C21—C22—C23 | 122.86 (12) | C35—C36—H36 | 119.9 |
C22—O22—H22 | 112.4 (16) | H1W—O1W—H2W | 107.4 (19) |
C21—C1—C11—C12 | 84.07 (14) | C1—C21—C22—C23 | 176.49 (11) |
C31—C1—C11—C12 | −50.38 (16) | O22—C22—C23—C24 | 157.55 (12) |
C21—C1—C11—C16 | −90.69 (13) | C21—C22—C23—C24 | −23.39 (18) |
C31—C1—C11—C16 | 134.86 (11) | C22—C23—C24—C25 | 49.45 (15) |
C16—C11—C12—O12 | 169.85 (11) | C22—C23—C24—C28 | 168.63 (12) |
C1—C11—C12—O12 | −4.92 (18) | C22—C23—C24—C27 | −71.20 (15) |
C16—C11—C12—C13 | −8.98 (17) | C23—C24—C25—C26 | −49.40 (15) |
C1—C11—C12—C13 | 176.26 (10) | C28—C24—C25—C26 | −168.19 (12) |
O12—C12—C13—C14 | 161.76 (10) | C27—C24—C25—C26 | 71.10 (15) |
C11—C12—C13—C14 | −19.32 (16) | C22—C21—C26—O26 | −171.09 (12) |
C12—C13—C14—C18 | 166.07 (11) | C1—C21—C26—O26 | 5.44 (19) |
C12—C13—C14—C15 | 46.85 (13) | C22—C21—C26—C25 | 7.23 (18) |
C12—C13—C14—C17 | −74.08 (13) | C1—C21—C26—C25 | −176.24 (11) |
C18—C14—C15—C16 | −168.56 (11) | C24—C25—C26—O26 | −158.78 (12) |
C17—C14—C15—C16 | 71.04 (14) | C24—C25—C26—C21 | 22.82 (18) |
C13—C14—C15—C16 | −50.06 (14) | C11—C1—C31—C32 | −24.09 (16) |
C12—C11—C16—O16 | −171.37 (11) | C21—C1—C31—C32 | −157.80 (11) |
C1—C11—C16—O16 | 3.74 (17) | C11—C1—C31—C36 | 163.50 (11) |
C12—C11—C16—C15 | 5.70 (17) | C21—C1—C31—C36 | 29.79 (16) |
C1—C11—C16—C15 | −179.19 (10) | C36—C31—C32—C33 | −0.46 (19) |
C14—C15—C16—O16 | −157.08 (11) | C1—C31—C32—C33 | −172.97 (12) |
C14—C15—C16—C11 | 25.73 (16) | C31—C32—C33—O33 | 180.00 (12) |
C11—C1—C21—C22 | 92.42 (14) | C31—C32—C33—C34 | 0.0 (2) |
C31—C1—C21—C22 | −132.51 (12) | O33—C33—C34—C35 | −179.85 (14) |
C11—C1—C21—C26 | −84.04 (14) | C32—C33—C34—C35 | 0.1 (2) |
C31—C1—C21—C26 | 51.04 (15) | C33—C34—C35—C36 | 0.2 (2) |
C26—C21—C22—O22 | 172.03 (12) | C32—C31—C36—C35 | 0.7 (2) |
C1—C21—C22—O22 | −4.55 (19) | C1—C31—C36—C35 | 173.30 (13) |
C26—C21—C22—C23 | −6.94 (19) | C34—C35—C36—C31 | −0.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···O26 | 1.09 (3) | 1.49 (3) | 2.560 (1) | 164 (2) |
O22—H22···O16 | 1.05 (3) | 1.62 (3) | 2.664 (1) | 171 (3) |
O1W—H1W···O16 | 0.92 (2) | 1.88 (2) | 2.795 (2) | 172 (2) |
O33—H33···O1Wi | 0.92 (2) | 1.76 (2) | 2.684 (2) | 174 (2) |
O1W—H2W···O12ii | 0.97 (3) | 1.90 (3) | 2.870 (2) | 175 (2) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C23H28O5·H2O |
Mr | 402.47 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 8.948 (1), 27.128 (3), 9.045 (1) |
β (°) | 94.30 (1) |
V (Å3) | 2189.4 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.70 × 0.65 × 0.45 |
Data collection | |
Diffractometer | Siemens CCD three-circle diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.941, 0.962 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 41555, 4836, 4088 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.641 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.115, 1.01 |
No. of reflections | 4836 |
No. of parameters | 283 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.31, −0.17 |
Computer programs: SMART (Siemens, 1995), SMART, SAINT (Siemens, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991).
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···O26 | 1.09 (3) | 1.49 (3) | 2.560 (1) | 164 (2) |
O22—H22···O16 | 1.05 (3) | 1.62 (3) | 2.664 (1) | 171 (3) |
O1W—H1W···O16 | 0.92 (2) | 1.88 (2) | 2.795 (2) | 172 (2) |
O33—H33···O1Wi | 0.92 (2) | 1.76 (2) | 2.684 (2) | 174 (2) |
O1W—H2W···O12ii | 0.97 (3) | 1.90 (3) | 2.870 (2) | 175 (2) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y, z. |
Some years ago, we have accidentally encountered the twinned crystal structures of two similar compounds bearing the bis-dimedone moiety: bis(2-hydroxy-4,4-dimethyl-6-oxo-1-cyclohexenyl)phenylmethane (Bolte, Degen & Rühl, 1997) and 2,2'-methylenebis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) (Bolte & Scholtyssik, 1997). Since these compounds can easily be prepared (Hünig et al., 1979) we have decided to synthesize various derivatives with the objective to find out if these are also twinned (Bolte et al., 2001). We hoped to find more twinned crystal structures in order to understand why some of these simple compounds containing the common bis-dimedone skeleton are twinned. Unfortunately, neither any of these nor the title compound, (I), turned out to be twinned.
The two cyclohexenone rings display envelope conformations with C14 and C24 deviating by 0.644 (2) and 0.653 (2) Å, respectively, from the plane of the remaining five ring atoms. Both apices are extended towards the phenyl ring. Two strong intramolecular hydrogen bonds are formed connecting the two cyclohexenone rings. The water molecule bridges two different molecules via its H atoms and acts as an acceptor for the H atom of the hydroxyl group of a third molecule.